AI Security Update

Legal Perspective on AI Security With Alyson Laderman

Someone told an AI chatbot that their lawyer was gaslighting them. In this episode, we talk about AI security in the context of the law and look at AI security from the legal perspective with Alyson Laderman. Alyson provides a lawyer's perspective on many of the emerging risks in AI security, whether you should use an AI tool for legal advice, and using AI as a starting point to figure out questions to ask. We also talk about instances where a woman used a chatbot to determine her lawyer was lying and how that actually ended up causing more harm when she got to court. Check out this episode for in-depth overview of AI security from a legal perspective.

AI Security for Small Businesses: UK Perspectives and Neurodiversity with Lisa Ventura

AI security is increasingly relevant for small businesses, where limited resources and fast-moving adoption can create unique challenges and opportunities. In this episode, Lisa Ventura joins the conversation to share UK-focused perspectives on how organisations can better understand and approach AI security in practice. We explore how neurodiversity contributes valuable strengths to cybersecurity teams, particularly in identifying patterns, managing complexity, and improving resilience in AI-driven environments. The discussion also touches on the realities small businesses face as they adopt AI tools, from governance considerations to everyday security awareness. Rather than focusing on hype, this episode looks at practical, real-world considerations shaping how AI security is understood and applied across the UK small business landscape. This conversation is for anyone interested in how AI security is evolving in real-world business environments, and the human factors that shape it.

The Companies House Breach: AI, Accountability & Human Judgment with Michala Liavaag

In this episode, we’re joined by UK-based cybersecurity leader Michala Liavaag for a focused, real-world conversation on what the Companies House breach teaches us about modern security, AI, and accountability. With a background as a classical pianist turned security strategist, and now founder of Cybility Consulting, Michala brings a distinctive, human-centered lens to cybersecurity. We dive deep into the Companies House breach, which was a devastating breach in the UK, unpacking what happened, where controls and oversight fell short, and why incidents like this highlight the importance of cybersecurity awareness and education. Michala explains why AI can support detection and efficiency, but cannot replace human judgment, especially in complex, high-stakes scenarios. We also talk about accessibility considerations when traveling at airports and navigating security checkpoints which are now augmented by AI. Grounded in a real incident and expert insight, this episode provides great advice for charities, non-profits, and leaders.

The Fake Baby That Hacked a Company: AI, OSINT & the New Face of Phishing with Hakeem Thomas

What if a simple baby photo could compromise an entire organization? In this episode, we sit down with cybersecurity professional Hakeem Thomas, a U.S. military veteran with nearly two decades of experience across penetration testing, digital forensics, incident response, and Zero Trust initiatives. Hakeem shares a real-world phishing campaign where AI-generated images—built from employee photos—were used to trick staff into clicking. The result? A highly effective social engineering attack that bypassed traditional red flags and exposed just how dangerous AI-powered OSINT has become. We dive into how attackers are now automating reconnaissance across thousands of sites in minutes, cloning identities, and crafting hyper-personalized attacks that are nearly impossible to detect. From fake baby photos to voice cloning and sock puppet accounts, the threat landscape is evolving faster than most organizations can keep up. But this isn’t just about tools—it’s about people. Why are these attacks so effective? And what does your digital footprint reveal to someone who knows how to look?

AI in Pen Testing, Education, and the Importance of Building a Network with Phillip Wylie

AI is transforming how we work—but with great power comes new security risks. Join Phillip Wylie as he breaks down the most critical lessons in AI cybersecurity, from everyday misconfigurations to the future of AI fluency in the workplace. In this episode, you’ll learn why building a strong security culture is essential, how AI can both enhance and complicate penetration testing, and why continuous monitoring and vigilance are the keys to protecting data in a rapidly evolving digital landscape.